This doctoral study was initiated to explore the relative importance of organizational issues in software process improvement. It is based on a pilot case study, a multiple case study of twelve organizations, and a quantitative survey among 120 software organizations. The findings from the investigations suggest that the key to successful learning is a continuous and simultaneous dialectic interplay between the knowledge that the organization has established over time, and the knowing of the organization’s members in their respective contexts. Also, the findings indicate that success depends critically on six organizational factors. Finally, the findings show that there are important differences between small and large software organizations, specifically in the ways in which they react to unstable and changing stimulus situations.